I’m here today with Caitlin Macy who’s an amazing novelist. A Yale graduate with an MFA from Columbia, Caitlin has contributed to “The New Yorker,” “The New York Times Magazine,” and “O, The Oprah Magazine” among others. Her three books called The Fundamentals of Play, Spoiled, which are stories, and now her recent release, Mrs., have received enormous praise. She lives in Manhattan with her husband and two daughters. Welcome to Caitlin.

Caitlin Macy: Thank you so much for having me.

Zibby: To jump right in, in the description on your website of your collection of stories called Spoiled, you say, “You turn an unsparing eye on affluent and educated women who nevertheless struggle to keep their footing in their relationships and life.” This is the overarching theme in so much of your work. How did you grow so fascinated with this particular group of women?

Caitlin: Our generation, more than any other that came before, we’re the meritocracy. It’s utterly a generational preoccupation. So many of us, my peers and I, grew up in either modest, or straightforward, straight-ahead, middle-class backgrounds. Through going to elite colleges — I think is one reason why our generation is obsessed with college admissions. Colleges became a springboard for people to jump — let’s not say jump class levels because class is more complicated and more of a complicated question — but at least jumped income stratas, some people a couple rungs up from their parents, some ten rungs up. There were so many opportunities for people who were so disposed to go to Wall Street, corporate law, Silicon Valley, the tech start-ups, Hollywood, etc. There were opportunities for people who wanted to that to go and make money.

You have women who either through their own careers or through in some cases marriage, marrying guys who followed a similar path, find themselves in places that are unfamiliar. Maybe those places have nannies and drivers and private school admissions where they weren’t living in places like that before. I’m using places loosely, obviously. What I find interesting is not so much the trappings, the black SUVs. That’s been done. That’s been done to saturation. I actually find it a tiny bit boring. The way in which the trappings of the lifestyle affect these women psychological and emotionally so that when they find themselves in these new worlds, how do they cope with it? Some cope brilliantly. For some, it’s quite anxiety producing. That’s why I’ve gotten stuck there and been focused on that for a while, because of our generation’s jump into unfamiliar footing.

Zibby: The way you contrast old versus new money, the WASP culture versus nouveau riche, particularly in Mrs. which is a story that takes place — we could probably paraphrase it better — a story that takes place on the Upper East Side of Manhattan among several different parent groups who come from different backgrounds. You tell it from the point of view of Gwen Hogan who is an outsider on the outside looking in, sort of a scientist, dropped in the middle of this craziness who has a, I wouldn’t say a judgmental view but more of a reserved — well, maybe a judgmental view of the whole New York City scene. There are these other families like Jed Skinker, who owns a bank and has been around forever, and then John Curtis, a wannabe who keeps making himself over to be different people and is ultimately a terrible guy.

Shining a light on these warring factions, these different groups, does that help elucidate the differences between all these classes? Take it from there. Sorry, random question.

Caitlin: I hope it does. It’s a funny moment. I love the phrase nouveau riche. It reminds me of the eighties and the fun of the eighties. It’s all but dead. For those people who have money, at this point most of it’s new. We’re not living in a Wharton world dominated by generational family fortunes. I’m tolling the death now of that world, that, for lack of a better word, WASP aristocracy. In Wharton’s novels you had the four hundred. Then there’d be this one outsider coming in who chafed against the societal rules, or who wasn’t quite on, and disobeyed the rules, or trying to get out, or in some other way posed a challenge to the society. Whereas now, for instance I’ve noticed on Instagram this hashtag — I don’t know if you, yourself, use it — of #NativeNewYorker.

Zibby: I have used that hashtag, actually.

Caitlin: It’s interesting to me. It’s a badge of honor. It’s a point of pride. If we had hashtags in Wharton’s time, everybody would be #NativeNewYorker or they wouldn’t be there except for that one character who shows up and turns the tables. Given that that’s now a smaller group, to the point that it’s a point of pride for people on Instagram and social media, that speaks to the fact that most of us are outsiders now. I always feel I have one foot in and one foot out. I don’t know where you draw the line. Who’s an outsider? Who’s an insider? This moment is a very different moment for Wharton. I’ve been thinking, as I’m sure we all have the last day, of a lot about Tom Wolfe. It’s even a very different moment from Bonfire of the Vanities.

There’s a really great article. I keep quoting it, and I’m not totally sure of the source. I need to Google it. I believe it was James Wolcott writing in “Vanity Fair.” He wrote this fascinating article, one of those things that you’re sitting in the doctor’s office and you pick up and then it’s seminal and you think, “What if I never sat in the doctor’s office?” He wrote this piece, unless I’m misattributing it, about how Bonfire was pre-Clintonian, Bill Clinton obviously the ultimate example of meritocracy. He grows up poor in a small town. He skyrockets because of education, gets to Yale Law, gets , becomes president. It was fascinating to me. I never thought about Bonfire as historical. To me, I was like, “Bonfire’s still current,” more or less. I’d read it in the eighties, and I hadn’t reread it. He points that there isn’t this meritocratic person. There’s Sherman McCoy, the WASP aristocracy. There’s the scrappy Jewish lawyer. There’s not the person who we all know — I would say most of my peers fit into this group — who got educated and then decided to get some sort of corporate job and live in New York.

At the same time, I have a little bit of affection, a little bit of nostalgia for that old world probably because it’s all personal. It’s always all personal. My dad’s family had been prominent in the nineteenth century. My dad’s father, at the beginning of the twentieth century, lost all of his money. My dad, he experienced the highs and the lows. He grew up in a big house in , New York, pretty much raised by servants. Then when his father lost all of his money, he marched him down to enlist in the Air Force. He went into the Air Force, into the Armed Forces as the lowliest of the lows, which is an enlisted man having grown up with chauffeurs and governesses. He experienced both sides. My dad, I certainly associate in some ways with that lost world. That’s probably in there too. Jed Skinker’s in there to note the passing of that world. He’s the last gasp of that world.

Zibby: That’s so interesting that that’s the vantage point that you’re coming into this. I was trying to figure out, “What is her fascination? How comes she keeps writing about all this? What it is? I feel like when writers keep going after the same subject, there’s some personal connection. That’s really interesting. Where did you grow up yourself?

Caitlin: I grew up in Groton, Mass, where the boarding school is. That was another element. I did go to boarding school. I didn’t go to Groton. My sister went there. Interestingly enough, my husband went there. There was also that. There was that world. My parents weren’t faculty, but in some ways they were associated. They had friend there. I spend a lot of time at Groton when I was young. A number of my friends were fac brats. That was another glimpse into this world. I had the funny experience of going to boarding school, as did my husband actually, both of us. I think we’re the only people in New York who went to boarding school, but on financial aid. It was the funny ying-yang of having a foot in two different worlds. Certainly, there was some personal investment in the theme.

Zibby: In Mrs. in particular you capture some really funny elements of the Upper East Side. I’m trying not to take offense. I’m not sure if you meant it. “Maybe I’m having Caitlin on the show and she hates me. She hates people from the Upper East Side. Maybe I shouldn’t let her in the apartment.” No, I’m kidding. You definitely capture some of the idiosyncrasies, maybe not just to the Upper East Side but certainly to the culture. This one quote you have, one of the characters, Marni, has a dramatic play date at the main character Philippa Lye’s house. You say, “I cannot explain the effect Marni’s recounting of the playdate had on us except to say that while we thought we would be happy to get the details, we were not. All the fun had gone out of it, not just out of gossiping but out of getting and spending. Perhaps a better way to put this is that for a couple weeks we all stopped googling ‘Hamptons real estate.’” I laughed out loud when I read that. That’s so funny. Some of the things you talk about are not even things necessarily that people talk about. Class is a very almost taboo subject that you confront head-on. You unearth all these unspoken differences or things. Your keen observational eye is pretty good. I particular enjoyed that.

I find in talking to people — I don’t know if you find this too — for so many of us in New York there are very few people who don’t occasionally think about leaving. Everyone’s like, “I love New York, but maybe I’ll look in Connecticut. I’d really love to live in California.” Do you feel that way? It’s hard living here.

Caitlin: Oh, yeah. I met my husband. He actually grew up in Spain, but he’s from Massachusetts. His family’s from Massachusetts. I’m from Massachusetts. I thought, “Done. We’re out of here. That’s it.” He would say gently, “What am I going do for a living?” It’s true. I swore I’d never move here. The jobs are here. I wanted to work in publishing. The jobs are here. Then, twenty-five years go by and you realize that you’re still here. You’re not leaving. It is your life. It’s a bit of surprise for someone who thought that I’d always end up back in small-town Massachusetts.

Zibby: Tell me about your publishing journey. You went to Yale. Since then, what has happened?

Caitlin: Right out of Yale I got a job working for a literary agent. She was a woman who was the Doyen of children’s book publishing. Pretty much her clients had started the YA genre. She represented S.E. Hinton, Suzie Hinton, Paul Zindel, Robert Cormier, all these seventies problem YA novels, Paula Danziger. Her name’s Marilyn Marlow. She was at Curtis Brown. I was super excited to get a foot in the door. I made $16,500 a year. I wasn’t living large. Again, I was able to have a head in a department on the Upper East Side on 67th and 1st. It was different times. My roommate paid $500 for the big room. She was paralegaling. I paid $400 for the small room. I got a bit lucky.

The way I ended up paying for my life, because I did go back and get an MFA Columbia after a couple years, was that the woman I worked for represented someone who wrote a series book for middle-grade readers called The Saddle Club. She was looking for ghostwriters. She hired me as a ghostwriter. The funny thing was that I got hired as a ghostwriter not because she had any idea that I had interest in writing but because I had been a horsey kid. I’d grown up riding. I knew how to slot in the right words and talk about palominos, and martingales, and things like that. I ended up writing thirteen Saddle Club novels. It paid my way through grad school, and then had a bunch of different jobs after grad school when I was trying to finish Fundamentals of Play, which I finally sold at the end of my twenties. Piecing it together with various jobs and cheap rents.

Zibby: You know the movie Tully that just came out? There was one movie — now I’m forgetting the name — Charlize Theron and the same writer and director did, and she was a ghostwriter for a children’s book series.

Caitlin: Yes! Young Adult. I loved it. I absolutely loved it. I completely identified with going back to your town and raging around or whatever. That was great. That was a very intelligent movie.

Zibby: Thought-provoking. In Mrs., another scene I want to ask you about. After hearing mothers complain that their kids wouldn’t wear their mittens, you talk about this main character Gwen who’s on the outside looking at this whole scene. You say, “She couldn’t imagine having that kind of adversarial relationship with her only child. Sometimes she would hear them addressing their nannies. ‘Why is she wearing those pants? What happened to the ones I laid out?’ as if motherhood were a battle which the toddlers were winning.” I have a three- and four-year-old. Sometimes is it easier to just send them in a tutu and ballet shoes than the pants or the skirt that I had in mind. The tone you have here suggests you might not agree with that decision. How could the kids actually exert that authority? What are you sayin’ about me here? Let’s talk about it.

Is this how you feel? Is Gwen a front for you? Is Gwen the anti-you?

Caitlin: It’s definitely Gwen. It’s funny. I had someone tell me, “Now I’m not going to call you Caitlin anyone. I’m going to call you Gwen Hogan.” I was flattered in a sense because everybody has their morally perfect observational narrator. I’m sure Fitzgerald would have loved to be as abstemious and correct and as perfect as Nick Carraway, but in fact he was descending into alcoholism. Gwen is one of these people who because she never has that debate that I have two or three times a day where you’re going, “My kid needs me, but I really want to have that glass of wine, and finish the crossword, and text my friend ten times.” You drag yourself up from that, “Yes? What it is?” You go and . Mine are older now. My younger one for an entire year didn’t believe in putting socks on. That was my equivalent of mittens. I feel like I know people like her — I will say it was more common in an older generation — who has almost an excess of self-control and never decides to sit on the sofa with a glass of wine when she should be cleaning up the apartment or helping her child. She really suffers from that because she’s unable to connect with the other moms.

How do we connect as mothers? Often it’s through shared confusion, complaint, sharing our challenges, and admitting how hard it is. She’s somebody who it’s almost not in her code to do that because of the way she was raised. She was raised in a harsh environment. It is a bit judgy. She’s almost portraying this, “Cannot compute. I don’t understand.” She’s one of those quietly on it, effective, efficient mothers and people who get it done. I think of her in the book as a good mother. I try to show different ways of being a good mother. I also think Philippa Lye is a good mother even though she would maybe be judged as the worst mother of all time but in fact truly loves her children. That, in a certain sense for Gwen, is handicapping. She can’t reach across the divide to say, “My kid threw a temper tantrum today.” Granted, in the book she does have an only child. That child is incredibly tractable. Sometimes you get an easygoing kid who’s willing to comply. In a certain sense it’s what isolates her from the front of the struggle.

Zibby: You have a sixth grader and a ninth grader. Your book just came out in February. How long did it take you to write Mrs.? Where did you do it? Did you work at home? Do you have an office? What was your routine in writing it?

Caitlin: It seems as if it took forever. I put the book down twice. I said, “I’m not finishing it. It’s not going forward.” I had this flash of insight. Originally, some of the book was told from the perspective of Philippa Lye. Every time I would get to that point in the book, eighty, a hundred pages in, I felt like I was hitting a wall. It was so deadly. The insight was that these crazy, damaged people are not that interesting from the inside. They’re more interesting from the outside to observe and remark upon. To actually go in someone’s head who’s crazy and damaged turned out to be a little bit boring. Once I realized that I had to excise her perspective from the novel, it started to go so much faster. I was able to finish it quite quickly. That was after several years of putting it up, putting it down. I did a few other things while I was writing it.

I’ve listened to other women on the podcast saying similar, but I’d love to say that I have a routine and I knock out my ten triple-space pages as I just read Tom Wolfe did every day, but it’s really hit or miss. Some days I feel super professional. After a fifteen- or eighteen-year wait, I finally got a maid’s room in our building. We have a pre-war apartment building. I live in a pre-war building that rents out these maid’s rooms. We were on the wait list forever. I figured I’d die before I got one. Then a couple people moved.

I set up the maid’s room as a home office, which has been a game changer. I’d like to say that I’m down there during school hours. It ends up being stealing two hours here and there. What I usually do that helps a lot is I go up to the Society Library on 79th and Madison. I go up to the fifth-floor writer’s room and stay there for a really long day or two per week. Those are inevitably my most productive days because I’m out of the house. I saw that article in “The Times” about procrastibaking. I don’t procrastibake, but I procrastitidy. I start tidying. With two kids — I can’t imagine four — with two kids there’s always something to do whether it’s order the shoes or book the doctor’s appointment. It ends up being a little bit of trying to get in a couple hours but not always making it.

Zibby: That’s encouraging. I had Jennifer Wallace on the other day. She gets up at four in the morning and writes before everybody gets up. Every night now I go to sleep thinking, “Should I try to do that? Should I try to set an alarm?” I can’t do it.

Caitlin: That’s so appealing to me. I flirt with that idea constantly. I’ve done it twice. It was amazing.

Zibby: I’m sure it’s amazing. By four o’clock in the afternoon I’ll be spacing out. On your website you had a link to one article you wrote in 1998 in the Live section of “The New York Times” where you wrote about “babysitting” — which you said more was hanging out, basically hanging-outing — babysitting for a fifteen-year-old boy in Manhattan whose mother was an actress and often not home.

Did your experiences with that babysitting moment in time inform more of these class distinctions? Was that your first intro into a specific type of lifestyle? Also, I need to know if you are still in touch with this boy and what has become of him. He sounded like a pretty awesome kid.

Caitlin: He was a great kid. Because I had gone to boarding school and college, I’d obviously, like all of us, spent a lot of time in living rooms of people who lived a certain kind of a life. I can say who it was. I’m happy to say who it was. I didn’t want to at the time. I worked for Blair Brown, who was fantastic to work for. What it actually was an introduction into the theater world, which I loved. I was always a theater kid. I’d been a theater kid when I was little. Blair gave me the habit. She was super generous giving me tickets. She gave me the habit of going to theater as an adult. Now it seems like it’s back. Maybe because of the musicals. I’m not sure. My daughter loves going to musicals, Evan Hansen and so on. There was this moment where people wouldn’t be caught dead in the theater. I had a friend saying, “It’s too stagey. It’s too slow. I can’t deal with it.” Being around theater people and going to plays was a real treat. If I could have chosen, I would’ve loved to be a playwright. I love the idea.

Zibby: It’s not too late.

Caitlin: Maybe I’ve got one in me. I love that idea of sitting at Sardi’s with the actors. I loved that whole world. That was interesting. Blair herself is a wonderful person. She paid me well. She put up with me. It wasn’t my finest hour as an employee. I had so much going on. I was struggling to pay the rent, and struggling to write, and dating, and in my twenties, post-college. It wasn’t my finest hour. They tolerated that. I’ve always felt that if her son wanted to get in touch with me, he could. I wasn’t going to stalk him. However, I did run into Blair recently because she has a house up in Cornwall, or somewhere up in Litchfield County near where we are on the weekends. We had a great time catching up and reminiscing. She’s in a bunch of stuff now. She was just in Orange is the New Black. She was doing a couple plays. She did that Uma Thurman play, which was a lot of fun. It was really fun to remember that moment in my life. Two years was encapsulated, then I moved on and we lost touch. It was nice to circle back. He was an amazing kid. I’d be really curious to know what he’s doing. If you’re listening…

Zibby: Do you have any advice to aspiring writers?

Caitlin: Yes. I probably have pages of advice. One thing that I found helpful was something someone told me. I was having those days where you’d sit down to write, and you’d be completely frustrated because everything was bad that came out. Try to do something that you approve of eighty percent rather than going for perfection. It can lower the bar and make you feel more able to take risks. Writers, we have our good taste. We start out incredibly judgmental of other writers, of ourselves. It’s very important to try to turn down the critical voice and get something on the page. The other side of that coin is you can’t give up. That’s basically it. So many people, when I was doing the MFA, we all came out thinking, “Oh, god. We’re never going to get there.” Then so many people published their books and have continued to publish. The persistence is eighty percent of the battle, to go back to the eighty percent again. That’s my main advice. Try not to be too critical. Keep going.

Zibby: I was just saying this to my husband on the street yesterday. We had this interesting meeting talking about what makes someone really successful. Sometimes it’s just doing it. Sometimes I read a book and I’m like, “I could’ve written that.” You know what? I didn’t. I wasn’t the one. I could’ve taken that picture. You know what? I didn’t take that picture. Some of it is literally I think as you’re saying, not that I have done it, but just in getting it done in some way…

Caitlin: What people don’t talk about it, there is inspiration. You have those great days where you feel inspired and it flows out of you. The inspirational moments, I find, they don’t just hit you walking down the street. You have to be struggling for a few days. Then you get a moment. You earn a moment. Suddenly it’s taking off. You feel, “Oh, god. I must be a total fraud if I’m not massively inspired each and every day.” The fact is once you’re sitting down and trying to do a routine as much as possible, then it sets the stage for inspiration to come. It allows inspiration to come. That was really good for me to observe here and there that, “That was an such easy day. I whipped through that scene,” or whatever it was, but it was because I’d done the preparation to get there. It’s not just drudgery or inspiration. It’s a bit of both.

Zibby: What are you working now? What’s comin’ next?

Caitlin: I’m working on a couple things. I’m working on a first-person novel about female friendship. It seems like since the Ferrante that’s what everyone’s doing now, jumping right in there. I’m also toying with a YA novel. They always want you to write YA because YA sells. Everybody’s, “Write YA. Write a YA.” I’ve never had an idea. I kept saying, “No. I’ve got nothing.” Suddenly I thought, “Wait a minute. I do. I do have an idea.” I haven’t started writing, but I’m mapping it out. I’m working on this first-person novel. It’s fun to be back to first-person, go back to where I started after doing stories and doing third-person. It’s nice to go home again.

Zibby: I’ll be looking for that. I can’t wait. Thank you so much for coming on “Moms Don’t Have Time to Read Books.” I really appreciate all your time.

Caitlin: Such a pleasure. Thank you, Zibby.